6-Azido- and 6-aminoflavins as active-site probes of flavin enzymes

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MASSEY, Vincent, Sandro GHISLA, Kunio YAGI, 1986. 6-Azido- and 6-aminoflavins as active-site probes of flavin enzymes. In: Biochemistry. 25(24), pp. 8095-8102. ISSN 0006-2960. eISSN 1520-4995. Available under: doi: 10.1021/bi00372a045

@article{Massey19866Azid-8471, title={6-Azido- and 6-aminoflavins as active-site probes of flavin enzymes}, year={1986}, doi={10.1021/bi00372a045}, number={24}, volume={25}, issn={0006-2960}, journal={Biochemistry}, pages={8095--8102}, author={Massey, Vincent and Ghisla, Sandro and Yagi, Kunio} }

<rdf:RDF xmlns:dcterms="http://purl.org/dc/terms/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#" xmlns:foaf="http://xmlns.com/foaf/0.1/" xmlns:void="http://rdfs.org/ns/void#" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/8471"> <dc:format>application/pdf</dc:format> <dc:rights>Attribution-NonCommercial-NoDerivs 2.0 Generic</dc:rights> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <dc:contributor>Yagi, Kunio</dc:contributor> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:43:55Z</dc:date> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/28"/> <dcterms:bibliographicCitation>First publ. in: Biochemistry 25 (1986 ), 24, pp. 8095-8102</dcterms:bibliographicCitation> <dc:language>eng</dc:language> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2011-03-24T17:43:55Z</dcterms:available> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dc:creator>Massey, Vincent</dc:creator> <dc:creator>Ghisla, Sandro</dc:creator> <dcterms:abstract xml:lang="eng">6-Azidoflavins have been bound to the apoproteins of five representative flavoproteins and their properties, before and after light irradiation, compared with those of the same proteins containing the appropriate 6-aminoflavin. In the dark the 6-azidoflavoproteins are quite stable, except for L-lactate oxidase, where spontaneous conversion to the 6-amino-FMN enzyme occurs slowly at pH 7. 6-Azido-FMN Old Yellow Enzyme is converted to the 6-amino-FMN enzyme by aerobic turnover with NADPH, and 6-azido-FAD D-amino acid oxidase is converted to the 6-amino-FAD enzyme by treatment with D-alanine. Light irradiation of 6-azidoriboflavin bound to riboflavin-binding protein does not result in any covalent fixation of the flavin to the protein. Light irradiation of 6-azido-FMN flavodoxin gives only a small amount of covalent linkage. In contrast, 6-azido-FMN Old Yellow Enzyme undergoes a very facile light-induced change, in which approximately 50% of the flavin is attached in a stable covalent linkage to the protein. The resulting flavoprotein form has lost the ability to bind phenols, a distinctive characteristic of the native enzyme; it does, however, bind NADPH, but the latter cannot reduce the covalently bound flavin. 6-Azido-FAD D-amino acid oxidase also undergoes a facile light modification, in which almost quantitative fixation of the flavin to the protein takes place. The resulting flavoprotein cannot bind benzoate, an active-site ligand for the native enzyme, nor is it reduced anaerobically by D-alanine. The covalent linkage is fairly labile and is destroyed on denaturation of the protein. 6-Azido-FMN lactate oxidase is also fairly susceptible to light irradiation; in this case, however, much of the change occurs in a dark reaction following irradiation. The product is readily reduced by L-lactate, in contrast to the results with D-amino acid oxidase. We have not yet been able to determine whether a covalent linkage occurs, although the evidence implies that a labile covalent linkage is formed, which is probably hydrolyzed in a subsequent dark reaction.</dcterms:abstract> <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/8471/1/6_Azido_and_6_aminoflavins_as_active_site_probes_of_flavin_enzymes.pdf"/> <dc:creator>Yagi, Kunio</dc:creator> <dc:contributor>Ghisla, Sandro</dc:contributor> <dc:contributor>Massey, Vincent</dc:contributor> <dcterms:issued>1986</dcterms:issued> <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/8471/1/6_Azido_and_6_aminoflavins_as_active_site_probes_of_flavin_enzymes.pdf"/> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/28"/> <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc-nd/2.0/"/> <bibo:uri rdf:resource="http://kops.uni-konstanz.de/handle/123456789/8471"/> <dcterms:title>6-Azido- and 6-aminoflavins as active-site probes of flavin enzymes</dcterms:title> </rdf:Description> </rdf:RDF>

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